Procedure:  1000 mL, 1-neck flask, stirbar, septum, condenser, N₂ inlet

                  Dissolved 15.967 g of I in 500 mL of DME.  Stirred at rt.  Added 1.984 g of (Ph₃P)₄Pd.  Added a solution of 12.056 g of II in 70 mL of EtOH followed by 60 mL of 2.0 M aqueous Na₂CO₃.  Refluxed.  After 18 h, TLC (10:90 EtOAc-hexanes, UV) shows product spot at Rf 0.59.  The reaction mixture was filtered through Celite and concentrated by rotary evaporation.  The residue was taken up in CH₂Cl₂, brine was added and the mixture was extracted.  The organic layer was dried over MgSO₄, filtered and the solvent was removed by rotary evaporation.  The product was isolated by flash chromatography on silica gel using 10:90 EtOAc-hexanes as eluant.  The product was a clear, colorless oil.

 

¹H NMR (CDCl₃, 300 MHz) d 8.13 (d, J = 7.7 Hz, ArH), 7.33 (m, ArH), 7.18 (d, J = 6.6 Hz ArH), 7.08 (m, ArH), 6.12 (s, NH), 2.10 (s, ArCH₃), 1.45 (s, C(CH₃)₃).